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From High School Sweethearts to Sailing Scoundrels: 53 Years of Love, Laughter, and a Little Chaos

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In 1952 a girl was born in Chicago to immigrant parents—with her whole life neatly laid out for her. She was to study hard and marry well—meaning she was supposed to wed a union electrician with an ‘A’ card (like her father). Once married, she was to have children and live a block or two away from her parents on the South Side. She was, in essence, supposed to live a life of wedded bliss boredom. 

Thus, her whole life was to be focused on two things—security and money. Successful people owned their own home—losers didn’t. And her hardworking parents clearly didn’t want their daughter to be a loser. They kept her on a tight leash—and only gave her an allowance of pennies. 

In order to earn some spending money, she began to sew custom doll clothes for her girlfriends. 

This isn’t easy for two reasons—one, doll clothes are small and, two, sewing machines don’t shrink to suit the project. It’s like using a large paint brush to draw a fine-lined postage stamp. 

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But she did, as requested, worked hard—not only at sewing but at everything else as well. She was a straight A student and a girl scout with a million merit badges. 

In many ways, she was the girl that every parent at Gage Park High School wanted their child to be—an exemplary student and an exemplary human being. 

Gage Park was a huge school. I think there were 1,000 people in her freshman class. I was one. But I didn’t make it. Not only did I leave early, but to my eternal embarrassment, I failed English, the only subject I cared about.  ;-(

Part of the reason was that I began working as a professional actor. But another reason was because, at 15 years of age, I purchased a William Atkins’ double ender—a 24-foot wooden sloop built in 1932. I paid $200 for her, every cent I had. Why so little? Because the in-the-water vessel had been broken into, looted, trashed, wrecked, and used as a gang hangout for illiterates. Illiterates? Yeah, they’d spray-painted the word FOCK inside the cabin—as well as pooping in the bilge and ripping up the interior to make a fire in the bilge in order to stay warm in winter.

Carolyn is a hard worker
Carolyn is a hard worker

I didn’t have any money after the purchase—so I considered what I could do to improve my brand new 36-year-old woodie besides replacing the seven rotten planks or sister the 12 rotten frames. Oh, and replace the engine and find a rig. 

My mother had just been given a bolt of fabric and she suggested curtains as a way of inexpensively sprucing up the old girl. 

So, I borrowed a spoon and returned to my vessel—to spoon out the feces in the bilges. 

Occasionally I’m paid to give talks at boat shows—once I was paid $5,000 for an hour’s work—and I always say, “First, spoon the feces out of your bilge—you shouldn’t circumnavigate until you do so!”

Good advice. 

But the second thing I did back in early 1968 was to contact Little Miss Goody-Two-Shoes about sewing me up some curtains… if she could find time from her job, merit badges, and advanced placement classes. 

The only thing she knew about me was that I was a drop-out who ran with the wrong crowd. (The only friends I had that hadn’t already OD’d were in jail!) 

When she came out to North Avenue and the north fork of the Chicago River to see the boat, she was totally puzzled. 

“Are you nuts?” she asked when she saw Corina. “Why? Why would anyone buy such a collection of lumber?”

“Oh, you know,” I said breezily, “to sail around the world, write a book about it, and live happily-ever-after.” 

“On this?” she laughed, looking at my boat. “Fatty, you can’t even stand up!”

It was true. Corina barely had sitting headroom—she lacked standing headroom by nearly two feet. 

I put the best spin I could on it by saying, “Well, if I wanted to stand tall with other rich yachts, perhaps this isn’t the best boat. But if I was, say, focused on horizontal activities… she’s freak’n perfect!”

Now I tell this story in two different ways—both of which are true. 

The first version is that she sewed my curtains and I didn’t have the money to pay her at the time. And the darn gold-digger has been hanging around for 55 years, two dozen hurricanes, a number of sinkings, and four circs to get her money. 

The second version, equally true, is that she kept coming down to re-measure the curtains—and to measure the mattresses, sail covers, etc. And I began to think that maybe she wasn’t so smart. I hadn’t even paid her for the first job and she was already on her fifth group of measurements. 

It was a hot day in August when she brought down the leeclothes she’d whipped up and we were both sweating as we fitted the canvas to the bunks. I decided to take off my tee-shirt (I had rock-hard abs back in those days) and while doing so I had an epiphany. There was somebody aboard that wasn’t too bright or perceptive—but it wasn’t my future wife, Carolyn.

What is in Your Sail Repair Toolkit

In Tonga, Carolyn studied basket weaving
In Tonga, Carolyn studied basket weaving

Now, of course, being a gentleman, I said, “Marry me! We’ll elope and sail down to the Caribbean—where your cement-shoe-toting Italiano parents will never be able to find us!”

“Ah, gee,” Carolyn said. “I’m only sixteen—and I’d like to finish high school before hearing wedding bells.” 

Of course, I thought to myself, “…how freak’n middle class! Am I sure I want to get hooked up with such a conservative thinker?”

Nonetheless I decided to wait for her—and as she returned to reality while I slipped free of it forever by sailing off into sea-gypsy-hood. 

I left for my summer cruise of the Great Lakes with 186 pennies and two ravenous crewmembers who’d just jumped bail—both so dumb, they viewed me as their meal ticket. Crazy!

On the other side of Lake Michigan from Chicago was a wealthy little town called Saugatuck that was filled with well-off teenage girls whose parents wanted to get them away from the bad boys of summer in Chicago—surprise!

I was a true hippie (still am) and thus I started making silver spoon jewelry which, darn it, sold too fast. Nonetheless, I told everyone I’d spend every penny I made each day by dawn tomorrow—and I kept scrupulously to that promise.  

In order to meet demand for my creations, I forced my customers to help craft their items. Soon, I was making money hand-over-fist which, unexpectedly, forced me to have a mammoth dock party each evening to burn away my profits with Boones Farm, Ripple, and far worse. 

Having a successful business boosted my ego—so I decided, as one does, to invent my own religion as well. I called it Green-Slime because the crude altar I’d constructed had burning/popping green slime (soaked in kerosene) from the harbor mixed with pieces of copper tube that glowed bluish green during the popping of the slime. 

Remember, this was 1969 and the Beatles were in India with a groovy spiritual guru—hoping to find a shortcut to God. That’s right—it was an oddly spiritual time, and if you don’t believe me—just ask Timothy Leary. 

Anyway, that evening as I was massaging green slime around on the body parts of a pair of blond twins, I had a full-on religious experience. It started with a heavenly noise, then a pulsating celestial (bluish) light from the cosmos—then FAR F’N OUT, God Himself spoke. 

I was gobsmacked!

“Put your hands in the air,” God said. “You are under arrest!”


Darn! It wasn’t God, it was the Saugatuck sheriff and his gun-toting lackeys.

Everywhere we sail, Carolyn learns a new skill
Everywhere we sail, Carolyn learns a new skill

And as he dragged me to the jail house with my entourage screaming that there was “no jail in the Midwest that could hold Fatty Goodlander.” Well, the thought entered my head that if Carolyn had been with me, perhaps I wouldn’t have been arrested?

Carolyn, meanwhile, was named valedictorian of Gage Park High and as such gave the keynote address during her 1970 graduation. However, Mr. Hahn, the principal of the school, was horribly paranoid. He demanded to see her speech—after all, this was during the height of the VietNam war—and pinko-commies were hiding under every rock.  

Luckily, her speech was mild—and even Mister Hahn couldn’t find anything to complain about as he returned the speech, neatly typed on green typing paper. 

Of course, when the big day came, Carolyn took out her green speech, waved it at the principal to see—then read her anti-war red speech as the principal howled, “Shut off the microphone! I want that miscreant’s head on my deck RIGHT NOW!”

But the moment she completed her speech, she tossed both copies in the air—and ran down the center aisle as fast as her little legs could carry her. 

I, by prearrangement, was tacking back and forth just off the Chicago waterfront. Carolyn banged out of the school at a full-tilt-boogie… and then, with a mighty leap… leapt over downtown… and landed with a graceful thud on my foredeck. 

“Trim, trim,” I shouted as we hardened up (on all levels) and lived happily ever after. 

That was 53 years ago and we just celebrated our 53rd anniversary. We’ve almost never been apart since those romantic days—through numerous sinkings and decades long spans of abject poverty—but not one single arrest. (Yes, it’s nice to be right.)

And she’s not just my wife—she’s my best friend, my lover, and mother to our wonderful child as well. We were so young when we hooked up. In a way, we raised each other during hundreds of thousands of sea miles, 53 years of living aboard, and four circs. I literally could not have become me (let alone stay out jail) without her. She’s immeasurablely improved my life—and I tell her that every single day, not merely on our anniversaries. 

Here’s the bottom line—I’ve only really done two things right in life—saying, “I” and “do” to Carolyn were both of them.

Fatty and Carolyn are still in Singapore with the daughter and two grandkids—shamelessly mooching off gullible members of the Changi Sailing Club. 

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Cap'n Fatty Goodlander
Cap'n Fatty Goodlanderhttp://fattygoodlander.com/
Cap’n Fatty Goodlander has lived aboard for 53 of his 60 years, and has circumnavigated twice. He is the author of Chasing the Horizon and numerous other marine books. His latest, Buy, Outfit, and Sail is out now. Visit: fattygoodlander.com

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